Organic photoelectric material containing benzoheterocyclic structure and preparation method and application of organic photoelectric material
A technology of organic photoelectric materials and heterocycles, which is applied in luminescent materials, photovoltaic power generation, organic chemistry, etc., can solve the problems of carrier transport difficulties, carrier accumulation, device efficiency reduction, etc., and achieve improved fluorescence quantum efficiency, high Fluorescence quantum efficiency, the effect of enhancing luminous brightness
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Embodiment 1
[0039] Example 1: The above compound 1 of the present invention can be synthesized by the following method.
[0040]
[0041] In a 500ml reaction flask, phenanthrenequinone (20.80g, 100mmol), 6-amino-1,4-benzodioxane (16.63g, 110mmol), 1-naphthaldehyde (17.18g, 110mmol), ammonium acetate (15.41g, 200mmol) was dissolved in 250g (based on the mass of phenanthrenequinone) and added to the reactor. Under a nitrogen atmosphere, the temperature was raised to 115°C for 8 hours. The liquid phase monitoring showed that there was no remaining phenanthrenequinone, cooled to room temperature, and washed with ethanol Beat once with ethanol:ethyl acetate at a volume ratio of 10:1 to obtain 40.20 g of the target compound with a yield of 84%. The quality is characterized as follows: mass spectrometer MALDI-TOF-MS (m / z) = 478.5514, the theoretical molecular weight is 478.5510; Anal.CalcdforC33H22N2O2 (%): C82.83, H4.63, N5.85, Found: C82.81, H4 .65, N5.85.
Embodiment 2
[0042] Embodiment 2: above-mentioned compound 22 of the present invention can be synthesized by following method.
[0043]
[0044]In a 500ml reaction flask, phenanthrenequinone (20.80g, 100mmol), 6-amino-1,4-benzodioxane (16.63g, 110mmol), 1-pyrenecarbaldehyde (25.55g, 110mmol), ammonium acetate (15.41g, 200mmol) was dissolved in 250g (based on the mass of phenanthrenequinone) and added to the reactor. Under a nitrogen atmosphere, the temperature was raised to 115°C for 8 hours. The liquid phase monitoring showed that there was no remaining phenanthrenequinone, cooled to room temperature, and washed with ethanol Beat once with ethanol:ethyl acetate at a volume ratio of 10:1 to obtain 44.21 g of the target compound with a yield of 80%. The compound is characterized as follows: mass spectrometer MALDI-TOF-MS (m / z)=552.6338, theoretical molecular weight is 552.6330; Anal.CalcdforC 39 h 24 N 2 o 2 (%): C84.76, H4.38, N5.07, Found: C84.75, H4.40, N5.06.
Embodiment 3
[0045] Example 3: The above compound 31 of the present invention can be synthesized by the following method.
[0046]
[0047] In a 500ml reaction flask, phenanthrenequinone (20.80g, 100mmol), 1,4-dimethyl-1,2,3,4-tetrahydroquinoxalin-6-amine (19.50g, 110mmol), 1- Anthracene formaldehyde (22.69g, 110mmol) and ammonium acetate (15.41g, 200mmol) were dissolved in 250g (based on the mass of phenanthrenequinone) of acetic acid and added to the reactor. Under a nitrogen atmosphere, the temperature was raised to 115°C for 8 hours, and the liquid phase monitoring There was no remaining phenanthrenequinone, cooled to room temperature, and beating once with ethanol: ethyl acetate with a volume ratio of 10:1 to obtain 43.26 g of the target compound with a yield of 78%. The compound is characterized as follows: mass spectrometer MALDI-TOF-MS (m / z)=554.6968, theoretical molecular weight is 554.6970; Anal.CalcdforC 39 h 30 N 4 (%): C84.45, H5.45, N10.10, Found: C84.44, H5.48, N10.08....
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